Declan Desmond makes a documentary highlighting the progress in the lives of several Springfieldians.

!! Tropes:
* BaitAndSwitch
** One of the children followed by the documentary becomes a successful laywer and doctor, but then loses her job and becomes the CrazyCatLady.
** As a mall photographer, Marge is shooting a picture for what appears to be a young Captain [=McAllister=], but when she plays disco music, he suddenly transforms into Disco Stu.
* BigNo: Smithers shouts several of these as a result of being tied up inside a grandfather clock and forced to hear the loud chimes.
* EveryoneWentToSchoolTogether: Many of Springfield's adult characters are seen at elementary school together.
* FunnyBackgroundEvent: While Homer sings his song to Desmond, a young Carl briefly appears behind him in Frink's time machine.
* FutureLoser: What the Crazy Cat Lady ends up being.
* GilliganCut: When Declan asks Homer and Marge if they're considering having kids, Homer said he wouldn't be caught with a couple of rugrats. The next scene is eight years later with Bart and Lisa as babies.
-->'''Homer''': [[LampshadeHanging You'd better not put this after the scene where I said I wouldn't have any kids]]. ''[[LampshadeHanging That]]'' [[LampshadeHanging would be a devastating edit]].
* MockMillionaire: Homer pretended to be wealthy to impress Declan but Mr. Burns unexpectedly showed up and ended the hoax.
* NeverTheSelvesShallMeet: Prof. Frink tried to tell his past self not to pursue a scientific career. He was ran over in the past, preventing him from getting young Frink's attention.
* OrphanedPunchline: "and that's how I got the vending machine contract for the Kremlin."
* RoyaltiesHeir[=/=]InventorOfTheMundane: Homer (falsely) claimed he became wealthy by inventing the condiment pen.
-->'''Homer:''' I got the idea from the regular pen.
* SelfMadeMan: The sort of wealthy man Homer pretended to be.